1,2-Dichloroethane → 1-Chloro-3-phenylpropyl phenyl carbonate

HRID 745036Notes

Reaction equation

Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[C:11]1([CH2:17][CH2:18][CH:19]=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1.[Cl:27]CCCl>>[C:2](=[O:3])([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[O:20][CH:19]([Cl:27])[CH2:18][CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 4

HCID 111,2-Dichloroethane

HCID 1049Pyridine

HCID 7707Benzenepropanal

HCID 15891Phenyl chloroformate

Product 1

HCID 194227691-Chloro-3-phenylpropyl phenyl carbonate

Conditions

Temperature: 80 °C

Procedure

Phenyl chloroformate (0.80 g, 5.1 mmol) and 3-phenyl-propionaldehyde (0.96 g, 7.2 mmol) were dissolved in 1,2-dichloroethane (5 ml) and pyridine (0.020 g, 0.25 mmol) was added dropwise to the stirred solution. Stirred at 80° C. for 2 days. Washed with water (10 ml), dried (MgSO4) and concentrated. Purified by flash chromatography (Silikagel 60, petroleum ether/ethyl acetate 95:5). Yield: 0.45 g 1H-NMR (CDCl3): delta=2.43 (CH2CH); 2.87 (CH2CH2CH); 6.34 (CH); 7.19-7.41 ppm (phenyl).

Workup

washWashed with water (10 ml)
dry with materialdried (MgSO4)
concentrationconcentrated
customPurified by flash chromatography (Silikagel 60, petroleum ether/ethyl acetate 95:5)

Sources & evidence

ORD record: ord-f04926b931ec42c181d42bcf958ddf5c
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559266

Reaction notes

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